Description:The Chestertown Historic District is the older section of Chestertown. It includes the central business district which is dominated primarily by late-19th and early-20th century commercial structures and includes a late-19th century courthouse; the river front which is lined by several 18th and early-19th century Georgian and Federal houses with several early-20th century houses across the street; several garages and 19th century low-income frame houses along Cannon Street, the middle class residential areas along Maple, High, and Washington. Sections of the Washington College campus are included in the northern area. Intrusions consist primarily of new or greatly altered buildings scattered throughout. The Chester River Bridge is not included in this nomination. In the area around High Street, Georgian, Federal, Gothic Revival and simple early tradesmen's dwellings predominate. The Washington Avenue area consists of large Victorian, Queen Anne, and Shingle Styles, with additional vernacular utilitarian homes and smaller 20th century bungalows. Washington College structures erected in 1844 and 1854, Middle, East, and West Halls, are the earliest remaining, with Middle being a Greek Revival building and East and West stylistically designed to compliment it. Reid or Normal Hall, across Washington Avenue, was originally a late Victorian dormitory with mansard roof, built in 1896. In 1929 a Mt. Vernon portico and additions were added, and later, stair towers were erected on each end. Other College buildings were erected from 1918 to 1970 in Georgian Revival are contemporary styles. Near the business district, along High and its cross streets, structures are constructed directly on the sidewalk with yards existing generally to the rear. The Washington Avenue and nearby residences are set back with landscaped yards surrounding the homes; while the college buildings center generally around an open green. Commercial use is generally located on a two block length of High Street, and two blocks, to the south, of Cross Street with residential units often located above these businesses. The commercial activities of Chestertown are housed primarily in vernacular buildings of modest scale, of types as required for their daily activities of the craft, trade, or sales, or social functions. The treatment of the facades, signs, and other public representations of the housed commercial activities have changed through time and are still changing, but the basic scale of the commercial streetscapes remains unchanged within the vernacular format. The inclusion of the several buildings of more studied design and architectural merit within the commercial areas does not here create unexpected or extreme contrasts of design or scale, and these inclusions tend to compliment the more numerous vernacular buildings in their relationship to the streetscape and to the day to day activities of the commercial areas. As one moves away from Water Street; along High Street, residences become more of those for the less affluent of the 18th and early 19th centuries, with later homes interspersing where possible and development on side and back streets. The Washington Avenue development opened a new neighborhood to those with ample funds to erect large, comfortable Victorian and later vernacular utilitarian residences. Streets off the Avenue developed again for less expensive and smaller residences of the same and later periods.

Significance:
The Chestertown Historic District is significant for the concentration of buildings that record the development and growth of this Eastern Shore town, Chestertown is the seat of Kent County and as such is and has throughout its history been a political, cultural, and commercial center on the upper shore area. In the 18th century the town was one of Maryland's wealthiest and most prominent towns. On a major route between Philadelphia and Virginia and the South, Chestertown had a college and an important Episcopal parish. Its citizens played leading roles in State and national affairs. By the 19th century and into the 20th the influence of Chestertown was limited primarily to the Eastern Shore. Within the district are numerous excellent examples of 18th, 19th, and early-20th century buildings of various types (commercial, residential, ecclesiastical etc.) of various styles (Georgian through Bungalow) some of which are the best examples found in the state. Such is particularly true of the 18th and early-19th century houses like River House and Widehall.

District Resources

Resources not specifically itemized in a list within NR nomination form.